Asymmetric Total Synthesis of (2R)‑Hydroxynorneomajucin, a Norsesquiterpene from Illicium jiadifengpi

We
report the first total synthesis of (2R)-hydroxy­norneomajucin,
a norsesquiterpene derived from the Illicium genus.
This natural product displays neurotrophic properties. Small molecule
neurotrophins have potential as therapeutics in neurodegenerative
diseases. Key steps of our synthesis include a Tsuji–Trost
reaction, a Pauson–Khand cyclization, and a Nagata hydrocyanation.
A simple sequence of reductions and a Mukaiyama hydration introduce
the A-ring substituents with the correct configurations. The overall
synthesis was completed in 17 steps (longest linear sequence, LLS).

本研究报告了（2R）-羟基诺美马祖辛的首例全合成，该化合物为来自川芎属的倍半萜类天然产物。该天然产物表现出神经营养活性。小分子神经营养素在神经退行性疾病治疗中具有潜在的应用价值。本合成过程中的关键步骤包括Tsuji–Trost反应、Pauson–Khand环化反应和Nagata氰化反应。通过一系列简单的还原反应和Mukaiyama水合反应，成功引入了A环取代基并确保了正确的构型。整个合成过程共完成17步（最长线性序列，LLS）。